2-Methyl-3-butyn-2-ol → 2-pentadecanone, 6,10,14-trimethyl-

HRID 1676155Notes

Reaction equation

HRID 1676155 reaction equation
CC(O)(C#C)C.[CH3:7][C:8]([OH:27])([CH2:11][CH2:12][CH2:13][CH:14]([CH3:26])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])C#C.[OH-].[K+]>>[CH3:26][CH:14]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:25])[CH2:19][CH2:20][CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:13][CH2:12][CH2:11][C:8](=[O:27])[CH3:7]

Participants

4

Reactant 3

HCID 82582-Methyl-3-butyn-2-olHCID 14797Potassium HydroxideHCID 1198673,7,11,15-Tetramethylhexadec-1-yn-3-ol

Product 1

HCID 104082-pentadecanone, 6,10,14-trimethyl-Yield 96.1%

Procedure

A 100 ml-four-necked flask equipped with a thermometer, a reflux condenser, and a stirrer was charged with 8.61 g (102) mmol 2-methyl-3-butin-2-ol (MBI) and 30.14 g (102 mmol) 3,7,11,15-tetramethyl-1-hexadecin-3-ol (DIP) stirred with 750 rpm and heated up to reflux temperature. After 5 min an internal temperature of 95° C. was reached, and 2 ml KOH (41.42% in H2O, 20.53 mmol) were added. The reaction was controlled by GC (samples were taken after 60 min, 155 min and 385 min). The ketones were separated by distillation. Yield acetone 5.8 g, (97.5%), yield 6,10,14-trimethyl-2-pentadecanon (C18—K) 26.1 g, (96.1%), not optimized.

Workup

  1. customA 100 ml-four-necked flask equipped with a thermometer, a reflux condenser, and a stirrer
  2. temperatureheated up
  3. temperatureto reflux temperature
  4. customwas controlled by GC (samples were taken after 60 min, 155 min and 385 min)
  5. customThe ketones were separated by distillation

Sources & evidence

ORD record
ord-607e22cbd9ff4ddc90b7b0a60b0382a3
Source dataset
uspto-grants-2011_08
Patent number
US08003843B2

Reaction notes

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